I was a late bloomer as far as punk rock goes, sorry to say. I didn't going to DIY shows until I was 19. I don't remember what the first show I went to was, I just remember not believing that anybody actually liked the music they were playing and being terrified of all the facial tattoos and filthy dogs. I got over all this in good time.
As far as the "scene" in Madison is concerned, it ebbs and flows. At its best you have everyone at the same party watching the same band and drinking from the same keg. At its worst everyone's at a different bar and you get a bunch of underattended shows. The nice thing about Madison's size is that it's too small to really sustain individualized DIY punk scenes (metal, hippie punks, crust punks, etc) so everyone tends to hang out under one roof.
Compared to three years ago, there are a fraction of the number of basements throwing shows in Madison which sucks a whole lot. It means that most shows are run through bars which makes them 21+ and more expensive to drink at. This summer the Madison Police Department prioritized busting "underground music clubs" and were shutting down basement shows listed on the internet before they began. This sucks, but I'm sure Madison will bounce back one of these days.